Sodium Hydroxide → (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:26])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:26])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl (2RS,3SR)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (4.85 g, 13.1 mmol) in methanol (20 ml) was added 1N aqueous sodium hydroxide solution (13.1 ml, 13.1 mmol), and the mixture was stirred at room temperature for 6 hrs. The reaction solution was evaporated under reduced pressure, diluted with 1N hydrochloric acid (50 ml), and extracted with ethyl acetate (100 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give (2RS,3SR)-3-(4-fluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (3.8 g, 84%).
Workup
- customThe reaction solution was evaporated under reduced pressure
- additiondiluted with 1N hydrochloric acid (50 ml)
- extractionextracted with ethyl acetate (100 ml×2)
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was recrystallized from ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-4ac072eb450542ddafb5e45ae9551018
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982348B2
Reaction notes
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